By Jon Friedman for Next Avenue

A few months ago, I received the kind of jolt from my tax preparer that many of us will get sooner or later. He informed me that he'd decided to retire in the coming years.

While I was happy for him, I immediately recognized the agonizing implications for me: that our 29-year association would be coming to an end and I'd need to find someone to take his place. Someone I could trust, afford and enjoy doing business with. Oh yes, compatibility would be crucial, too.  

His bulletin threatened to upend my life, the same way similar news from a long-time doctor, dentist or lawyer might. Finding a new specialist can be a major challenge and a potential point of stress or anxiety.

How would I go about the search?, I asked myself.

Suddenly, I had to start thinking about a new tax preparer's expertise and track record and I had to fret about how much I might be paying.

Don't we all settle into our little comfort zones, based on years or even decades of a professional relationship which — if you're lucky — morphs into a friendship?

The Strong Bonds With Our Pros

As we age, there's great solace in knowing that these pros will be there for us. They've come to know us, our histories and our idiosyncrasies (and we know theirs).

Based on the long association, we hope they''ll give us preferential treatment when necessary: appointments on a moment's notice and call backs without delay to answer questions whether mundane or critical. And maybe, just maybe, they'll even give us a friendly discount on their services based on our years together.

The fellow who has been doing my taxes annually and I go back a long way — all the way to 1992. He'd been working on my taxes since George H.W. Bush was President, Phil Simms was the quarterback of my beloved New York Giants and New York Yankees great Derek Jeter was still a high school phenom in Michigan.

And now I'd have to find someone just as trustworthy, wise and knowledgeable of both the tax code and my unique financial life. Could I succeed in finding someone every bit as reliable?

A Wrenching Decision

The truth is, there's no easy answer when you have to look someone in the eye and make an assessment that could affect you for years to come, perhaps the rest of your life.

Even specialists like doctors, dental surgeons, accountants and lawyers acknowledge that this can be a wrenching decision.

If you're lucky, the retirement of one of these pros is a planned event, so you have time to choose a replacement.

Referrals and Recommendations

Often, physicians and dentists reassign their patients to the care of a partner or someone local they know and respect.

"In my case, I discussed my departure with three other solo practicing pulmonologists and asked if they'd be willing to accept my patients," said Dr. John Pellicone, a pulmonary specialist who launched his New York City practice more than three decades ago and retired in 2015. "I then contacted each of my patients and requested that they indicate to which physician their records should be sent.

Dr. Paul Bizzigotti, an orthopedic surgeon in Cadillac, Mich., said: "A personal recommendation carries the most weight, My patients know they can trust my reputation and that I have their best interests at heart."

This type of effort makes the hand-off easy, but it makes no allowance for matching the patient's personality with the new medical maven.

In addition, selecting a new physician of dentist means ensuring that he or she is in network for your insurance plan.

The Questions to Ask

And there are other questions you need to ask, as Pellicone pointed out: "Are the office hours of the new provider practical? Is the office conveniently located? Who provides coverage for the new provider when he or she takes time off? If the patient requires hospitalization, will the new provider come to the hospital for a bedside visit or is the practice solely office-based?"

It's helpful to do your own research when your pro is nearing retirement. But a word-of-mouth reference from someone you trust can be key.

That could help you know whether their expert's personality would be a good fit for you.

I'm lucky. I have had the same general physician since the 20 century. When he has looked me in the eye and told me, "You need to lose weight," I took it as constructive criticism and not a personal rebuke, based on our long association. (Thanks, Doc: I lost 40 pounds two summers ago!)

But one day…well, I don't want to think about it.

Let's face it. We're bound to feel skittish the first time we enter the office of a new specialist for us.

"You can get intimidated," acknowledged Mark Diamond, an attorney in Brooklyn, N.Y. who recently had to find a dental surgeon to replace the one he'd been using for 30 years.

Fortunately for Diamond, he found a new dental surgeon referred by his retiring one and is pleased — he trusts the man's expertise and the office is a short drive away.

I'm happy for him. Now, if you'll excuse me, I have to start finding a nearby tax preparer. April's just around the corner.

Jon Friedman, the author of Forget About Today: Bob Dylan's Genius for (Re)Invention, Shunning the Naysayers, and Creating a Personal Revolution (2012, Penguin's Perigree Imprint) is a lifelong journalist and a dedicated educator.

©2021 Next Avenue